


You Plannin' on Askin' Me Out?

by captain_americano



Category: Supernatural
Genre: Asshole!Cas, College AU, Cute, Fluff, M/M, Slight pining?, for once in my life I actually had my work beta'd, hipster!cas
Language: English
Status: Completed
Published: 2014-07-21
Updated: 2014-07-21
Packaged: 2018-02-09 18:41:18
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,604
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1993665
Author URL: https://archiveofourown.org/users/captain_americano/pseuds/captain_americano
Summary: <blockquote class="userstuff">
              <p>Asshole/Hipster Cas is my favorite so here's a little piece of whatever this is.</p>
            </blockquote>





	You Plannin' on Askin' Me Out?

**Author's Note:**

> Thanks to Kayli-San, who beta'd this for me!

Dean hitched his scarf up to cover his ears and nose, bracing himself against the bitter winter chill as he opened his dorm's front door and headed down the hallway to the miserable outside world. He glared at the gloomy, grey sky and cursed his objectively exceptionally good looking roommate, Balthazar, for always sneaking girls into their dorm and kicking Dean out for an hour or so. Lately he'd taken to guys as well so his encounters were more frequent and they'd do a couple of rounds.

Being kicked out was precisely the last thing that Dean wanted to have happen to him on such an abysmal Friday afternoon, so close to the closing time of his favourite on-campus café. He trudged through the thick fallen snow for five long minutes, his leather laptop bag slung over his shoulder, before reaching the café. He shouldered the door open and hurried inside out of the cold, right into a big, ugly purple sweater.

"Watch it, Losechester," the sweater appeared to have someone in it, a rather rude some with a deep, gravelly voice that Dean totally did not find sexy.

"Sorry," Dean mumbled, avoiding the sweater's piercing blue glare and stumbling over to one of the few unoccupied tables, dumping his laptop and coat there. He dodged in and out of the crowd, picking his way to the counter where he ordered a cinnamon latte and he would never, ever admit to his younger brother Sam that he occasionally indulged in such drinks.

Just as he slumped into his chair, his heart sank as he heard the closing bell ring.

"Alright, everyone get out!" He heard a bubbly southern accent – Jo. "You don't have to go home but you can't stay here," the owner's daughter called, making her way over to Dean as the crowd cleared out.

"Kick it, Dean, I have a date tonight and mom left me here alone to close." Jo gently pushed Dean's shoulder, ignoring his glare and wearing a big grin.

"So Benny finally asked you out, huh?" Dean smirked, not moving.

"Uh-huh, so get out!" Jo whined. Dean tapped his paper cup thoughtfully.

"If I clean and lock up, can I stay a bit longer? Please Jo?" He asked his best friend, looking up through his thick lashes. "My roommate kicked me out again so he could get laid and I'm freezing."

"You know that look doesn't work on me, Winchester," Jo sighed and handed him the keys. "I'm only sayin' yes because I really have to go!"

Dean watched her jog out the back. "Nothing has changed since last time you closed,” she called, “so remember to lock the back door as well. Don’t stay here all night, even if that couch is comfier than the dorm beds.” She walked back out, holding a large brown coat. “And don't you even think about eating those cookies," she said sternly, kissing him on the forehead and running out. Dean rolled his eyes and opened his laptop bag, making use of the free Wi-Fi before cleaning.

Dean was just signing out of Facebook to get started on his essay when the door swung open, sending in a blast of freezing night air. He looked up and blushed as Purple Sweater re-entered the cafe, texting on his Blackberry. Dean recalled that the guy refused to buy an iPhone because they were "too mainstream", and immediately felt creepy for remembering such a menial detail about an almost complete stranger.

Anyway, what the hell was Cas even doing in the café? Didn't be realise it was closed? Dean shook his head and ignored the guy, attempting one of his many essays while he still had some time to kill. He became so absorbed in his own bull-shitting that he almost forgot he wasn't alone.

"Oh, my fucking God, isn't anyone going to take my order?" Dean started and looked up, realising he probably shouldn't have let him in.

"Café's closed, Cas, so no, no one is gonna serve you," Dean said quietly, focusing on his laptop. He heard footsteps and felt the air next to him shift as Cas helped himself to a seat right at Dean's table.

"I'll bite,” Cas asked disinterestedly. “What are you doing in here?" Dean shook the bite comment from his mind, getting ready to tell Cas off when he finally looked up and met the man's otherworldly blue eyes. He faltered.

"I, uh..."

"Wow, you really are the idiot I took you for,” Cas laughs. “I mean, you can't even speak properly!"

"Damn it, Cas, why are you such a jerk all the time?" Dean asked.

"It's the only way to find out who people really are," Cas shrugged, sinking into his chair.

"Oh," Dean said stupidly, thinking. His heart sank a little. "So, by being a jerk to me, you found out I'm an idiot?"

Cas peered at him for a long moment before sighing. "I don't know, depends on if you know how to use that coffee machine or not," he said, jerking his head to the counter.

Dean grinned in spite of himself and headed to the machine. "What do you want?"

"Spearmint latte," Cas called from across the café, texting once again.

"You know, just because you're a dick doesn't mean you dot have to have manners. I mean, I am the one prepping something you're presumably about to consume," Dean said, receiving a one-fingered salute in reply. Dean took the coffee over to Cas and returned to the counter.

"So, uh, got any plans for tonight?" Dean asked, beginning to clean the coffee machine.

"Why, you planning on asking me out?" Cas didn't even bother looking up from his phone. Dean wasn't, right that second, but he'd definitely considered the possibility of doing so over a hundred times before. He wondered if Cas had ever considered the same thing, if he'd say yes or laugh in Dean's face, if he was waiting for Dean to make the first move, if he was being sincere or joking, if, if, if-

"Earth to Winchester!" Cas snapped. Dean looked up, confused.

"What?"

"Fuck, lucky you're pretty, 'cause you're really not that bright!" Cas scowled and walked over to the counter.

"Oh, sorry, I zoned out," Dean said, "my roommate kicked me out because he wanted to have sex."

Cas huffed in annoyance, but instantly perked up.

"Oh, right, your roommate is Balthazar. Mm, I'd love to share a room with him, he's so fucking hot," Cas said, staring off into the distance.

"Great,” Dean said sarcastically, “you and I can swap dorm rooms and you can have lots of sex with Balthazar and everyone else in this damn college."

"I don't have sex with everyone else here," Cas said quietly, looking hurt for a brief moment. He paused. "Whatever. Thanks for the coffee, I guess." He put a crumpled bill on the counter and turned to leave.

"Wait, Cas?" Dean blurted out.

"What?" Cas said impatiently. Dean hesitated.

"Uh, have a good night," he said, cringing at himself. Cas nodded and rolled his eyes.

"You too, Losechester," he replied, but Dean could swear he heard a tinge of affection. It was enough for him to grin like an idiot as he finished cleaning and got back to his essay.

+

The following Monday morning, Dean was stuck staring at the back of Cas' messy head for the majority of his architecture lecture. He was fantasizing about running his fingers through it, tugging on it lightly... Dean shook his head, attempting to change his focus and staring at the wall, the roof, the space between his desk and the floor. The staring at Cas was probably slightly, completely, totally and utterly unhealthy.

"Mister Winchester, I suggest you leave before the next class starts," the professor called and Dean was jerked from his reverie, looking around to find the room all but empty.

"Sorry, sir." Dean gathered his belongings and ran out of the lecture hall. He slowed as he got out the door and came face to face with Cas.

"Hey, Cas," Dean said, staring.

"Winchester." Cas nodded. "You busy later?"

"Why?” Dean asked, quoting Cas. “You plannin' on askin' me out?"

"Yes, I can no longer ignore the throbbing of my heart," Cas deadpanned. Dean rolled his eyes and made to walk off, surprised to find Cas falling into step with him.

"What're you doing? Quit following me!" Dean said harshly, aiming to be ruder than this douchebag. That he totally didn't have a crush on.

"Woah, someone woke up on the right side of the bed! Keep up the attitude and you might just have a shot with me," Cas smirked. Dean didn't respond beyond a blush that couldn't be helped. "God, don't be such a girl, are you actually going to give me the silent treatment? Fuck, fine, I'm sorry. I'd sleep with you any day of the week."

"You flatter me," Dean said cooly, unable to tell if Cas was being sarcastic or not, ignoring the jolt in his chest. "What is it you want, Novak?"

"I definitely like this side of you," Cas said, more to himself than to Dean. He cleared his throat. "I wanted to ask if you'd set me up with Balthazar."

"Ask?" Dean repeated, ignoring the flare of something unpleasant inside him. "You're asking me? Not telling me to?”

“Mhmm,” Cas said, looking amused.

“Why can't you do it?” Dean scoffed, “all that confidence bullshit flowing out of you and you can't even go to the other man-whore yourself?"

"If you're gonna get your panties in a knot, you can just forget it,” Cas teased. “No need to be jealous.”

"I’m not jealous of that idiot, let me tell you,” Dean said. He sighed. “Fine, if you want VD so bad, I'll set the two of you up.” He paused, turning to face Cas. “But don't come crying to me when he breaks your heart. Or, y'know, that mechanical device that pumps your blood around.”

"Thanks, Dean, you're the best,” Cas said. “I'll come around to your dorm at four." Cas bounced up onto the balls of his feet to give Dean a quick peck on the cheek before flouncing off, becoming lost in the crowd, leaving Dean to lightly touch his burning cheek in wonder.

+

Dean wondered if he should tell Balthazar or just let Cas show up and leave them to it. The thought of the two of them fucking so close to where Dean slept was both horrifying and heartbreaking, but as much as Dean liked avoiding any contact with his roommate, he felt inclined to tell the asshole. And get out of the place as soon as he could.

"You know that kid, Cas?" Dean said, a few minutes to four.

"Yes," Balthazar lied, looking up from his laptop.

"Whatever,” Dean said. “He's coming over at four and he wants to have sex with you."

"Is he good looking?" Balthazar asked. Dean rolled his eyes and sighed.

"Extremely."

"Wait, I know him, he's that asshole hipster, right?" Balthazar opened his mouth to go on but was interrupted by a knock on the door. Dean got up and yanked the heavy wood open.

"Pot," Dean said, indicating Balthazar, "Meet Kettle." And he pushed past Cas, leaving them to do whatever it was that he didn't want to think about.

Dean wandered aimlessly, not particularly wanting to go to his regular haunt that was always filled with cheery people. He headed towards the pond in the lonely cold, sweeping the snow off the bench with his bare hand and sitting down. Dean sighed at the frozen water.

He hated Balthazar, sure, and was constantly annoyed at being kicked out, but this was the first time he was actually jealous of the bastard. He didn't even know why he liked Cas so much. The guy was an asshole, but he was the realest guy Dean had ever met; never conforming, never people-pleasing, just being himself one hundred percent of the time. It didn't hurt that, when his talking didn't get in the way, he was one of the most aesthetically pleasing people to ever grace the Earth.

"Dean?"

"Hey, Jo," he said, without looking up. "How was the big date?"

"Really great, actually. Benny is just like a big teddy bear and--"

"Aw, no, c'mon, Jo, he's one of my best friends!” Dean groaned. “I don't need to picture him walking around with Piglet-” Dean paused. “Oh, my God, Jo, you're Piglet!" He burst out laughing, earning him a smack from Jo.

"Shut up, Winchester,” Jo said, grinning. “What's been going on with you?”

A moment passed.

"Have you ever liked a complete asshole?" Dean sighed.

"Everyone has," Jo said, wrapping an arm around him. "This isn't about that Cas, still, is it?"

"Right in one." Dean looked at her, his shoulders drooping.

"I don't think he's a complete asshole," Jo began. Dean stared at the ground again, unconvinced. "He’s just… guarded – maybe he's not what you think."

"What I think,” Dean said, “is that he's fucking Balthazar as we speak. What I know is that he came around with that intention, which is why I'm here." Dean chuckled, the sound forced and foreign. "We've talked a couple of times now, and each time is worse than the last.” He paused. “I actually fought back a bit, the last time."

"Ouch,” Jo said.

“Mhmm,” said Dean.

“Say you two did have a chance,” Jo said, “how could you even look at him if he got with Balthazar?"

"I don't think there's much 'if' about it," Dean replied, quiet.

"C'mon, come to the café,” Jo grinned. “I'll make you some hot cocoa with mini marshmallows.”

"Oh, I'm sorry, did we go back in time to when we were seven?" Dean teased. Jo rolled her eyes.

"Sure, trying to act all grown up and manly,” Jo laughed, her brown eyes shining, “but five bucks says you cave and add more than three.”

"You're on," Dean growled and the shook.

+

"Hey, kids, I'm glad you're here," Ellen said as Jo and Dean entered the kitchen. "Bobby had an accident at the auto-shop and he needs me to take him to the hospital."

"Woah, Ellen, is he okay?" Dean asked.

"Yeah, he's fine. Idiot cut off a finger." Ellen rolled her eyes. "You two can keep an eye on things, right? It ain't too busy out there."

"Of course, mom, go help Bobby," Jo said, voice calm, smiling at her mother. Ellen kissed them both on the forehead and ran out. There was a ding from the bell on the front counter and Jo asked if Dean could take care of it while she got the cocoas took the muffins out of the oven, all that jazz. Dean walked out of the kitchen and into the piercing stare of Cas.

"Jesus, you really are following me," Dean grumbled, picking up a pen and the order book.

"You wish, Winchester."

"That was awfully quick, Cas, couldn't lover-boy get it up?" Dean smirked, smile hollow.

"Why, you wanna know if you need to buy him a little blue pill before you meet up with him later?" Cas suggested.

"Oh, hey, Cas," Jo said as she brought out the tray of fresh muffins. "Hope you're not being too hard on poor Dean--" Dean let out a noise of indignation before Jo continued in a stage whisper, "--He's a little sensitive at the moment."

"Of course not, Miss Harvelle.” Cas replied, smirking. “Any friend of yours is a friend of mine.” He bowed his head politely.

"What can I get you you?" Jo asked, flashing her winning smile. Dean was completely confused by the exchange.

"I'll have a soy cappuccino please, Jo, in a mug, if you will,” Cas said. “And one of those delicious smelling muffins." Dean could not find a hint of insincerity or sarcasm in Cas’ voice.

"Coming right up, Cas!"

Dean followed Jo out the back and marvelled at her. "How'd you do that?"

"He's scared of me," Jo smirked. "Always had been. No clue why, but it's awesome."

"That is awesome," Dean replied, picking up his cocoa and adding one, two, three, four, five, six mini marshmallows and happily handing the five dollars to Jo. "Best fiver I ever spent," he shrugged and Jo giggled. She instructed Dean to give Cas his order, doing her best to play wing-woman.

"Soy cap, blueberry muffin,” Dean said, setting the order down on Cas' table. “Can I get you anything else?"

"Dean, Balthazar and I didn't have sex,” Cas blurted out. “I didn’t want him.” Since when did Cas blurt? Dean peered curiously at him, who was staring up at Dean with those bright blue eyes.

"Okay," Dean replied, wondering whether he was telling the truth or not.

Cas furrowed his brow and looked away. "I don't know why I told you that."

Dean shrugged for lack of a better response and returned to his cocoa, his marshmallows sufficiently melted on the top of the drink.

"He said that he and Balthazar didn't do it," he hissed at Jo. "I have no idea why he told me that!"

Jo shook her head. "Well, it looks like you've got things under control here, so I'm just gonna--" She went to walk off.

"Hey, what are you doing? You can't just leave me here alone with him!” Dean said. “There aren't any other customers and, damnit, this is your mom's shop!"

"Oh, don't be such a baby!" Jo exclaimed, indicating to herself. "Ultimate wing-woman."

And she was gone. Dean sighed and dampened a cloth to wipe down the tables. He glanced at Cas who was (surprise, surprise) texting, and occasionally picking at his muffin or sipping his coffee. Dean ignored him and went about his work.

"Hey, De-- uh, Winchester, c'mere for a second!" Cas called, snapping his fingers.

"I'm not a dog, Cas," Dean huffed, but walked over nonetheless.

"Pull up a seat," Cas indicated the chair across from him, which Dean promptly sank into. "Can I ask you a question?" Cas' voice was more vulnerable than Dean had ever heard. Not that it meant much. Really.

"I guess..."

"Dean." That was probably the first time Cas had ever used his first name. "What do you...” he shook his head. “You called me a slut, basically. Is that what people really think of me?"

"No, of course not," Dean responded truthfully. "Hipster asshole? Yeah, definitely. But not a slut, man."

"So, you don't think of me as a slut?" Cas asked, watching Dean. Dean knitted his eyebrows together in confusion.

"No, I don't,” Dean said. “Cas, since when do you care what people think of you? You're the most self-assured guy I know. And I mean that in a good way," Dean added quickly, as a tinge of hurt flickered across Cas' face.

"I don't care what people think, but for some reason,” Cas said, “I find myself caring what you think. It's quite annoying, really." Cas sighed. Dean sat silently for a moment, letting those words sink in. When Dean didn't respond, Cas continued, "I think that's why I didn't have sex with Balthazar.” He paused. “And why I wanted you to know."

"Why do you care what I think?” Dean asked harshly. “You've only ever been a jerk to me.”

"I know. But somehow, despite that, you're able to sit and have a conversation with me, and help me, and you're a decent guy," Cas said, and fuck, if that didn't make Dean feel worse than ever. The guy he'd been mooning over for the past year and a half just 'decent guy’d' him.

"Right, so, uh,” Dean said, “I'm not sure what I'm supposed to do with that.”

"Weren't you planning on asking me out?" Cas smiled, and it was genuine. Not a sarcastic grin, or a snide smirk... A genuine, semi-hopeful smile. It was beautiful.

In a moment of sheer bravery and very little thought-process, Dean responded, "Yes."

Cas' smile widened and it gave Dean more confidence. "Cas Novak, will you go on a date with me?"

"News flash, Losechester," he said with definite affection this time. "This is a date."

"So that means," Dean slid his chair closer and gently took Cas' pliant hand, "that I can do this?" Dean leant in close and stared into those deep blue eyes, so much deeper than he ever realised. Cas moved closer too, noticing Dean's light freckles that matched the flecks of brown in his green, green eyes.

Their lips met and their eyes fluttered closed. Against Dean's expectations, Cas let him take the lead and hurriedly opened his mouth, letting Dean explore the warmth. One hand still grasping Cas', Dean slid his other hand up Cas' back and wound his fingers in his hair, just how he'd imagined earlier that day.

Cas had one hand gently resting on Dean's hip and was letting out delicious little sounds, completely lost in the overwhelming feeling of Dean. He was no longer the guarded, rude boy whom Dean had despised being infatuated with, but was now a gentle, kind man who had decided to let Dean, of all people, in. Dean pulled out of the kiss and immediately regretted it, but placed his forehead against Cas'.

"I've wanted to do that for so long," Dean admitted.

"Creep," Cas chuckled.

"Jerk," Dean said.

"I'm your jerk, if you'll have me," Cas whispered, insecurity washing over him once more. Dean kissed his forehead.

"You're mine," he growled. Cas laughed, learning in to kiss Dean again.

**Author's Note:**

> It was recently brought to my attention that despite my username I've only ever posted SPN fic, so I'm working on my first 'official' Avengers fic c: watch this space!


End file.
